1. Field of the Invention
This invention pertains to novel S-aryl N-cycloalkylthiolcarbamates, particularly those in which the cycloalkyl has from three to six carbon atoms. A particular example being S-4-methoxyphenyl N-cyclohexylthiolcarbamate. This invention also relates to the method of controlling plant pests with these compounds, particularly pea aphids.
2. Description of the Prior Art
Plant pests such as insects, continually affect the growth of crops, trees, and other desirable vegetation. One method of controlling insects is by application of chemicals which affect the insects. These chemicals are applied to the soil, to the desirable plant, or directly to the insect itself. Because thousands of different insect species exist which differ in tolerance to chemicals, new chemicals must be discovered which are effective to control the deleterious effects of insects.
The prior art shows that certain thiolcarbamates are active against plant pests. The following patents and references illustrate the different thiolcarbamates claimed to be effective against certain plant pests.
U.S. Pat. Nos. 2,977,209 and 3,265,563 disclose S-phenyl N-alkylthiolcarbamates, S-chlorophenyl N-alkylthiolcarbamates, S-ethoxyphenyl N-allylthiolcarbamate, S-ethoxyphenyl N-alkylthiolcarbamates, S-p-tolyl N-alkylthiolcarbamates, and S-2,4-dimethylphenyl N-alkylthiolcarbamates as herbicides and fungicides. U.S. Pat. No. 3,632,332 discloses S-4-methylbenzyl-N,N-diethylthiocarbamate as a herbicide for rice fields. U.S. Pat. No. 3,301,885 discloses S-substituted phenyl N-alkyl, N-alkoxythiolcarbamates as herbicides, miticides, and insecticides. U.S. Pat. No. 3,687,653 discloses trifluoromethylbenzyl N-alkylthiolcarbamates as herbicides. U.S. Pat. No. 3,046,189 and Canadian Pat. No. 789,575 disclose S-alkyl N-alkylthiocarbamates as nematocides. R. Reimschneider and O. Lorenz, in Monatsch., 84, 518 (1953) describe S-phenyl N,N-dimethylthiolcarbamate, and D. G. Crosby and C. Niemann, Journal of American Chemical Society, 76, 4458 (1954) describe S-phenyl N-cyclohexylthiolcarbamate, and S-phenyl N-phenylthiolcarbamate. Netherlands Pat. NO. 6,606,753 discloses S-phenyl N-trifluoromethylphenylthiocarbamate and S-substituted phenyl N-substituted trifluoromethylphenylthiocarbamates as anthelmintics. M. S. Newman and H. A. Karnes, Journal of Organic Chemistry, 31, 3980-3983 describe S-.beta.-naphthyl N,N-dimethylthiolcarbamate, S-2-nitrophenyl N,N-dimethylthiolcarbamate, S-3-nitrophenyl N,N-dimethylthiolcarbamate, S-2,4,5-trichlorophenyl N,N-dimethylthiolcarbamate, S-3-trifluoromethylphenyl N,N-dimethylthiolcarbamate, S-2,3,5,6-tetramethylpentyl N,N-dimethylthiolcarbamate, S-4-tert-butylphenyl N,N-dimethylthiolcarbamate, S-2-methoxyphenyl N,N-dimethylthiolcarbamate and S-4-methoxyphenyl N,N-dimethylthiocarbamate. U.S. Pat. No. 3,932,632 discloses insecticides of mixtures of dithiophosphate compounds mixed with S-aryl N,N-dialkylthiolcarbamates, or S-aryl N,N-dialkylenethiolcarbamates, or S-aryl N,N-dialkynylthiolcarbamates, S-aryl N,N-(alkyl, alkylene, or alkynyl), (alkyl, alkylene, or alkynyl)thiolcarbamates, where the aryl may be a substituted phenyl.